Enantiospecific access to 10-N-substituted camphors

Tetrahedron

Volumn 61, Issue 3, 2005, Pages 599-601

  García Martínez, Antonio ^a   Teso Vilar, Enrique ^b   García Fraile, Amelia ^b   De La Moya Cerero, Santiago ^a   Díaz Morillo, Cristina ^b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

Author keywords

Alkylations; Amides; Amines; Camphor; Chirality; Enantiospecific synthesis

Indexed keywords

10 (PIPERIDIN 1 YL)CAMPHOR; 10 ACETYLAMINOCAMPHOR; 10 DIETHYLAMINOCAMPHOR; 10 TRIFYLOXYCAMPHOR; AMIDE; AMINE; CAMPHOR DERIVATIVE; NITRILE; NORBORNANE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS; WAGNER MEERWEIN REARRANGEMENT;

DRYOBALANOPS;

EID: 10044258613     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.11.006     Document Type: Article

References (26)

1. T.-L. Ho Enantioselective Synthesis: Natural Products from Chiral Terpenes 1992 Wiley New York
2. J. Seyden-Penne Chiral Auxiliaries and Ligands in Asymmetric Synthesis 1995 Wiley New York
3. A. Koskinen Asymmetric Synthesis of Natural Products 1998 Wiley Chichester
4. W. Oppolzer Tetrahedron 43 1987 1969
5. H.-U. Blaser Chem. Rev. 92 1992 935
6. An interesting review on the preparation of camphor derivatives is: T. Money Nat. Prod. Rep. 1985 253
7. K.-S. Yang, and K. Chen Org. Lett. 2 2000 729
8. K.-S. Yang, J.-C. Lain, C.-H. Lin, and K. Chen Tetrahedron Lett. 41 2000 1453
9. C.-H. Lin, K.-S. Yang, J.-F. Pan, and K. Chen Tetrahedron Lett. 41 2000 6815
10. C. Chapuis, A. Kucharska, and J. Jurczak Tetrahedron: Asymmetry 11 2000 4581
11. K.-S. Yang, and K. Chen J. Org. Chem. 66 2001 1676
12. C.L. Fan, W.-D. Lee, N.-W. Teng, Y.-C. Sun, and K. Chen J. Org. Chem. 68 2003 9816
13. J.-F. Pan, and K. Chen Tetrahedron Lett. 45 2004 2541
14. T. Mino, S. Hata, M. Sakamoto, and T. Fujita Tetrahedron Lett. 42 2001 4387
15. C.-W. Chang, C.-T. Yang, C.-D. Hwang, and B.-J. Uang Chem. Commun. 2002 54
16. P. Schenonne, A. Tasca, G. Bignardi, and L. Mosti Eur. J. Med. Chem.-Chim. Ther. 10 1975 412
17. S. de la Moya Cerero, A. García Martínez, E. Teso Vilar, A. García Fraile, and B. Lora Maroto J. Org. Chem. 68 2003 1451
18. A. García Martinez, E. Teso Vilar, A. García Fraile, S. de la Moya Cerero, C. Díaz Morillo, and R. Pérez Morillo Synlett 2004 134
19. For example see: W. Oppolzer, and R.N. Radinov Tetrahedron Lett. 29 1988 5645
20. Ketopinic nitrile can be obtained easily from fenchone by a single-Wagner-Merwein-rearrangement-based methodology: A. García Martínez, E. Teso Vilar, A. García Fraile, S. de la Moya Cerero, J.M. González-Fleitasde Diego, and L.R. Subramanian Tetrahedron: Asymmetry 5 1994 1599
21. A. García Martínez, E. Teso Vilar, A. García Fraile, S. de la Moya Cerero, and P. Martínez Ruiz Tetrahedron: Asymmetry 9 1998 1737
22. On this kind of ring expansions leading to bridgehead carbocations, see: R.C. Fort Jr. G.A. Olah P.v.R. Schleyer Carbonium Ions Vol. IV 1973 Wiley New York Chapter 32
23. J.J. Ritter, and P.P. Minieri J. Am. Chem. Soc. 70 1948 4045
24. L.I. Krimen, and D.J. Cota W.G. Dauben Organic Reactions Vol. 17 1969 Wiley New York 213 325
25. (c) García Martínez, A.; Martínez Álvarez, R.; Teso Vilar, E.; García Fraile, A.; Hanack, M.; Subramanian, L. R. Tetrahedron Lett. 1989, 30, 581.
26. Highly-reactive triflyloxyl group makes its nucleophilic substitution to be the main process, avoiding a possible competitive (undesired) Grob-like fragmentation (on this synthetic problem, see reference 7b and other references cited therein).